What are mistakes product managers make when trying to get buy in for their roadmap that end up damaging stakeholder relationships?

The biggest mistake I will mention here is not getting stakeholder buy-in. A lot of times we make assumptions about what people want and do not take the time ahead of to understand needs. Speak to those needs and share any constraints. Work to bring alignment across stakeholders. In the end, stakeholders lose trust in the product manager because they do not feel seen or heard. It is important that pre-work is done ahead of time so that when roadmaps are being presented, nothing comes as a surprise.

It seems all too easy to NOT get roadmap buy-in. Sometimes, it can feel like the default answer is always "No" at first, and despite all the work you have done, you are getting sent back to the drawing board.

Some things that help, not in any particular order:

• Go as wide as possible early on as pre-work to understand stakeholders' motivations and identify any possible opposition
• Dig deep to identify the true source of the opposition. Listen a lot, ask questions. Treat this exercise as part of requirements gathering.
• Identify dependencies early
• Tie roadmap item to financial impact upside
• Is the impact estimate credible and defensible
• Is the level of effort astronomical, or disproportionate to value
• Is there a downside, beyond the lost oportunity of not doing the feature
• Tie roadmap to broader strategy
• Are you potentially missing technical or other considerations?
• Have you been transparent and collaborative? Is anybody going to oppose the roadmap because they were excluded from discussions and decisions
• Get exec buy-in in smaller forums, early, even at the conceptual level
• Build a coalition of active supporters - there is safety in numbers
• Assume positive intent
• Seek to educate not sell
• Seek common ground
• Consider earlier conversations as setting the stage and foundation for later decisions. Aim to first not get a "no", rather than pushing for an immediate "yes"
• Give yourself enough time to work iteratively through to buy-in.

Not Understanding and/or Aligning OKRs

If you are operating against different and even competing OKRs then your roadmap will never get buy in. This issue creates the conditions where no matter what you have on there, there will not be alignment because everyone is chasing a different outcome. This is why OKR creation with stakeholders is critical - everyone needs to be bought into the direction before you can cuss and discuss the details and the how to get there

Not Framing the Story with Data

Your roadmap should not start with the actual details of the delivery items. You need to start with the consumer/customer/user opportunities (aka problems) that you have discovered through copious conversation, looking at your product metrics, and competitive analysis. Then you can talk about what outcomes you can drive by addressing these opportunities, THEN show what you intend to go discover or deliver. When you omit the opportunities and outcomes that are informed by your first hand data, then you make all your decisions subjective. This doesn't remove disagreement, but it changes the nature of the conversation to be "ok, lets take a step back and see what data best supports these differing opinions."

Just Saying No

To be clear, you need to say no a lot, but you just cant say "no" and move on. The best approach here is to always refer to the roadmap and ask the question "is this new thing more important than the direction we are already aligned on?" You have to remember that you probably can see the roadmap in your dreams at night, but your stakeholders don't, even if you publish it and you are transparent, the reality is that its not front and center each and every day for them like it is to you. Creating the habit of asking questions like the one above is real important to giving you the credibility to say no to low priority stuff, because you are saying yes to high priority stuff

From personal experience, I've made a couple mistakes that I can share:

1. Not doing enough research or having answers to pushback readily available (this makes you look weak and degrades trust in your recommendation or ownership).

2. Pushing an objective without understanding the other perspectives or priorities of stakeholders (this makes you look unprepared and degrades trust and collaboration).

Ways to mitigate these:

1. Spend your time to prepare your roadmap with lots of research (customer, prospect, field, data, market, competitive etc.) Work with your manager or peers to brainstorm or identify gaps in your roadmap in advance. Make your roadmap and reasoning bulletproof and well documented.

2. Spend time with stakeholders who are involved on a one-to-one basis to understand their current priorities and their perspective of your area and what they think is a top priority. Truly consider their perspective, they may have a point - people can tell when you aren't actually engaging with their perspective. Ask a bunch of questions to deeply understand. This allows you to prepare to present why you're moving in the direction that you're moving instead of their alternative path proactively and have a meaningful discussion about it. In addition to building a deep understanding of their perspective, building a strong relationship with stakeholders allows for you to have a basis of human connection to build from and tackle misalignment together.

It's crucial to ensure you’ve identified and engaged with stakeholders (including your own engineering team) correctly, to mitigate the risk of damaging relationships. Here are some common mistakes I’ve seen that can create friction with your stakeholders:

1. Failure to have a clear vision or strategy.  Understanding the destination and how you’re going to get there is key to prioritizing your roadmap and helping explain why behind those priorities.

2. Poor Communication. A lack of communication is as bad as an inability to successfully communicate as it leaves your stakeholders unaware or confused.  Ensure that you’re communicating in a clear and concise manner with different stakeholders, to ensure that they are both informed and understand the ‘what’ and ‘why’ behind your roadmap.

3. Lack of Stakeholder Input. Be sure to understand who the stakeholders you need to engage with are, and ideally before finalizing your roadmap (particularly for the near-term outcomes) get their feedback.  If they want more, ask simple questions like what they would reprioritize and why, and what they are willing to not get if you were to accommodate their ask.

4. Overpromising and under-delivering: It’s important to work with your engineering team and other stakeholders involved in the delivery chain (e.g., professional services teams) to ensure that what you’re presenting can be delivered in the timeframe you’ve suggested and get into the hands of your customer.  Without this you risk eroding your trustworthiness and the confidence that your stakeholders may have in you.

5. Lack of clarity on the outcomes being delivered.  While features may be the focus of many conversations (particularly with technical stakeholders), it’s important to portray the outcomes and benefits that what you’re delivering will help achieve. Many roadmap slides contain short text items, and so think though what additional content (e.g., a single slide or one pager) that can help portray the details behind what’s being delivered to help convey the ‘why’, the benefit, and how this will help your stakeholders communicate that value to end customers.

6. Failure to identify or communicate risks.  A roadmap is not a commitment, and yet many will view it that way.  Especially for items further out on your roadmap, the confidence in those being delivered on time decreases, often because problem or solution discovery has not been completed.  Acknowledge the risks and outline mitigation strategies to demonstrate thorough planning.

This is not an exhaustive list, and I’m sure you could add many other items from your own experience, but they do represent common pitfalls that many run into.  Good luck in getting alignment with, and buy off from, your stakeholders on your roadmap!